GB1298508A - Novel tetracyclines - Google Patents

Novel tetracyclines

Info

Publication number
GB1298508A
GB1298508A GB27595/70A GB2759570A GB1298508A GB 1298508 A GB1298508 A GB 1298508A GB 27595/70 A GB27595/70 A GB 27595/70A GB 2759570 A GB2759570 A GB 2759570A GB 1298508 A GB1298508 A GB 1298508A
Authority
GB
United Kingdom
Prior art keywords
methoxy
chloro
octahydro
dioxo
butyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB27595/70A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Research Corp
Original Assignee
Research Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Research Corp filed Critical Research Corp
Publication of GB1298508A publication Critical patent/GB1298508A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/757—Unsaturated compounds containing a keto groups being part of a ring containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/36—One oxygen atom
    • C07D263/42—One oxygen atom attached in position 5
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1298508 Tetracyclines RESEARCH CORP 8 June 1970 [12 June 1969] 27595/70 Headings C2A and C2C Novel tetracyclines of the formulµ wherein R 1 is H or OH, R 2 is H or halogen, R 3 is H or CH 3 , R 4 is dimethylamino or benzamido, and R 5 is H or C 1-4 alkyl are prepared by condensing azlactones or thiazolones of the formulµ with the appropriate methyl 3-oxoglutaramate, and, if desired hydroxylating the resulting products, converting the benzamido groups present into dimethylamino groups, removing the methoxy group at the 10-position, and the protective group on the amide nitrogen. The following intermediates are prepared: methyl 8 - chloro - 5 - methoxy - 4 - oxo - 1,2,3,4- tetra - hydro - 2 - naphthoate, methyl 8 - chloro- 4,4 - ethylenedioxy - 5 - methoxy - 1,2,3,4- tetrahydro - 2 - naphthoate, 8 - chloro - 4,4- ethylenedioxy - 2 - (2 - hydroxyethyl) - 5 - methoxy - 1,2,3,4 - tetrahydronaphthalene, 8- chloro - 2 - (2 - cyanoethyl) - 4,4 - ethylenedioxy - 5 - methoxy - 1,2,3,4 - tetrahydronaphthalene, 8 - chloro - 2 - (2 - formylethyl)- 5 - methoxy - 4 - oxo - 1,2,3,4 - tetrahydronaphthalene, 4 - [2 - (8 - chloro - 5 - methoxy- 4 - oxo - 2 - naphthyl)ethylidene] - 2 - phenyl- 2 - oxazolin - 5 - one, N - t - butyl - 4 - benzamido - 7 - chloro - 1,4,4a,5,5a,6,11,12a - octahydro - 3,12 - dihydroxy - 10 - methoxy- 1,11 - dioxo - 2 - naphthacenecarboxamide, N- t - butyl - 4 - benzamido - 7 - chloro - 1,4,4a,5,- 5a,6,11,12a - octahydro - 3,12,12a - trihydroxy- 10 - methoxy - 1,11 - dioxo - 2 - naphthacenecarboxamide, N - t - butyl - 4 - amino - 7- chloro - 1,4,4a,5,5a,6,11,12a - octahydro- 3,12,12a - trihydroxy - 10 - methoxy - 1,11- dioxo - 2 - naphthacenecarboxamide hydrochloride, and N - t - butyl - 7 - chloro - 4 - dimethylamino - 1,4,4a,5,5a,6,11,12a - octahydro - 3,12,12a - trihydroxy - 10 - methoxy- 1,11 - dioxo - 2 - naphthacenecarboxamide hydrochloride.
GB27595/70A 1969-06-12 1970-06-08 Novel tetracyclines Expired GB1298508A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US83268169A 1969-06-12 1969-06-12

Publications (1)

Publication Number Publication Date
GB1298508A true GB1298508A (en) 1972-12-06

Family

ID=25262345

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27595/70A Expired GB1298508A (en) 1969-06-12 1970-06-08 Novel tetracyclines

Country Status (11)

Country Link
AT (1) AT307392B (en)
AU (1) AU1532070A (en)
BE (1) BE751830A (en)
CA (1) CA926389A (en)
DE (1) DE2028705A1 (en)
ES (1) ES380657A1 (en)
FR (1) FR2052959A1 (en)
GB (1) GB1298508A (en)
LU (1) LU61109A1 (en)
NL (1) NL7008573A (en)
ZA (1) ZA704006B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7825105B2 (en) 2002-07-12 2010-11-02 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7825105B2 (en) 2002-07-12 2010-11-02 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds
KR101089429B1 (en) * 2002-07-12 2011-12-07 파라테크 파마슈티컬스, 인크. 3, 10, AND 12a SUBSTITUTED TETRACYCLINE COMPOUNDS
US8481513B2 (en) 2002-07-12 2013-07-09 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds

Also Published As

Publication number Publication date
NL7008573A (en) 1970-12-15
CA926389A (en) 1973-05-15
DE2028705A1 (en) 1972-02-17
AT307392B (en) 1973-05-25
FR2052959A1 (en) 1971-04-16
AU1532070A (en) 1971-12-09
BE751830A (en) 1970-11-16
ES380657A1 (en) 1972-10-16
LU61109A1 (en) 1970-08-12
ZA704006B (en) 1971-01-27

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees